Oxalyl chloride → HCID 25256390, compound

HRID 336275Notes

Reaction equation

HRID 336275 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:22])=O)=[CH:16][C:15]=1[N+:23]([O-:25])=[O:24].O[N:27]=[C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[O:36][C:37]([F:40])([F:39])[F:38])[NH2:29].CCN(C(C)C)C(C)C>>[CH3:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[O:22][N:29]=[C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36][C:37]([F:38])([F:39])[F:40])[N:27]=2)=[CH:16][C:15]=1[N+:23]([O-:25])=[O:24]

Participants

5

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 2794708N'-hydroxy-2-(trifluoromethoxy)benzenecarboximidamideHCID 594958102'-Methyl-2-nitro-[1,1'-biphenyl]-4-carboxylic acid

Product 1

HCID 25256390HCID 25256390, compound

Procedure

Oxalyl chloride (118 μL; 1.40 mmol; 3 eq.), Intermediate 22 (120 mg; 0.47 mmol; 1 eq.), Intermediate 2 (103 mg; 0.47 mmol, 1 eq.) and DIEA (103 μL; 1.40 mmol; 3 eq.) were reacted according to general procedure 2. Purification by column chromatography c-hexane/ethyl acetate, 90/10) afforded the title compound as a yellow oil.

Workup

  1. customPurification by column chromatography c-hexane/ethyl acetate, 90/10)

Sources & evidence

ORD record
ord-4d09dd2d0295449896ed5af33b8345ed
Source dataset
uspto-grants-2014_11
Patent number
US08889668B2

Reaction notes

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